Upgrading operating system versions on a large computing system including a plurality of computers performing a plurality of different server roles can be a very challenging process. Certifying that all necessary software runs correctly on an upgraded operating system requires testing all necessary software on the operating system in all required configurations, a process that is complicated, time consuming, and difficult to track. This creates a problem where timely upgrading of the operating system does not happen, leaving the computing system devices open to vulnerabilities that are fixed in the new version.